The Claisen Condensation

In this reaction, two molar equiv of an ____

ester combine to produce a β-ketoester.
One equiv serves as the nucleophile (enolate) and the other is the electrophile
which undergoes addition and elimination. The reaction is driven to product by the
final deprotonation step.

O
O O O
EtO
O CH2 +
O CH3 O CH3
H
H

O O

O CH3
a β-ketoester
Mechanism of the Claisen Condensation
O O
EtO O O
+ O CH3
O CH2
O CH3
H
pKa = 15.9 EtOH
The position of the equilibrium [pt]
EtO for the first three steps lies EtO
[pt] toward the starting ester. The
O O
overall reaction is driven to
EtOH
completion by the acid-base
reaction between the ethoxide O CH3
and β-ketoester.
O H H pK = 10.7
O [Eβ] a

O CH2 EtO
O CH3

[AdN] O O
O
C OEt
O
O CH2 CH3
an ester enolate a tetrahedral intermediate
 Mixed Claisen Condensation

Like mixed aldol reactions, mixed Claisen condensations are useful if

differences in reactivity exist between the two esters as for example when
one of the esters has no α-hydrogen. Examples of such esters are:

excess